Harold a



Patented Nov. 3, 1925.

UNITED STATES PATENT orrlce.

HAROLD A. LEWIS, OF WOODBURY, NEW JERSEY, ASSIGNOR TO E. I. DU PONT DENEMOURS &, COMPANY, OF WILMINGTON, DELAWARE, A CORPORATION OF DELA-WARE.

EXPLOSIVE COMPOUND AND PROCESS OF PRODUCING SAME.

N 0 Drawing.

To all whom it may concern:

Be it known that I, HAROLD A. LEWIS, a citizen of the United States, anda resident of \Voodbury. in the county of Gloucester and State of NewJersey, have invented certain new and useful Explosive Compounds andProcesses of Producing Same, of which the following is a specification.

My invention relates particularly to a process for producing a newexplosive of advantageous character and the product thereof. The objectof my invention is to provide a new and useful explosive compoundsuitable for use in detonators and so-called booster charges. My processfurnishes a simple and economical means of producing explosives of thenitro-nitrate class where the nitric ester side chain is attached to.the benzene nucleus through oxygen.

I have discovered that the condensation product of a nitro-chloraromatic compound with a polyhydric alcohol nitrates readily in thepresence of sulphuric and nitric acid, forming an aromatic compoundhaving a plurality of nitro groups attached to- .the ring and a sidechain comprised of a nitric ester of an aliphatic alcohol attached tothering through oxygen. For example, if I condense dinitrochlorbenzene witha dihvdric alcohol such as ethylene glycol, I obtaindinitrophenoxy-ethanol which on nitration yields trinitrophenoxy-ethylnitrate. Other glycols such as propylene and trimethylene glycol can betreated in the same manner yielding the correspondingtrinitrophenoxyalkyl nitrates, such substances constituting valuableexplosive compounds. Likewise dinitrochlorbenzene condensed with apolyhydric alcohol such as ylcerol gives dinitrophenoxy-glycerol, w iichon nit-ration gives trinitrophenoxy-glycerol dinitrate. Although theexact details of the various steps of my process may be varied, I

have found the following to yielda very satisfactory explosive compound,starting with dinitrochlorbenzene and ethylene glycol 100 parts byweight of 2, 4-dinitrochlorbenzene are dissolved in 322 parts by weightof ethylene glycol. To this is added an ethylene glycol solution of NaOHmade by dissolving parts of NaOH in 12 parts of water and adding322-parts of glycol. The

Application filed January 26, 1925. Serial No. 4,961.

mixture is heated at 90 to 100 C. for hour, during which time sodiumchloride crystallizes out. The hot mixture'is then drowned in about 600parts of water and the dinitrophenoxy-ethanol separated. 100 parts byweightof this product, after drying, are then dissolved in 1000 parts byweight of 95% sulphuric acid and the solution slowly added to 300 partsof nitric acid (1.47 sp. gr.) which is constantly agitated and kept at35 C. The temperature is then raised and kept at to for one hour, afterwhich the mixture is drowned in water and the crystalline productseparated and washed by any one of the well known methods; The crudeproduct obtained by me in following the process, as described above,gave a product melting at 10l102 C. \Vhen recrystallized fro-m benzeneit melted at l05106 C. The nitrate nitrogen as determined by nitromet/enwas 4.23% as compared with the theoretical value of 4.40% fortrinitrophenoxyethyl nitrate. The product flashed when heated on a steelspatula and detonated when primed with fulminate of mercury.

Trinitrophenoxy-ethyl. nitrate, as produced by my process, isparticularly well adapted for use in blasting caps or in socalledbooster charges, or in any of the numerous explosive devices for whichsuch explosives as trinitrotoluene, picric acid and tetryl have provedadapted. For example, in a blasting cap shell, I have found that acompressed charge consisting of 3 grains of trinitrophenoXy-ethylnitrate in the base of the shell, and a primer of t grains of a 90-10mixture of fulminate and chlorate with a superimposed inner capsuleexhibits an explosive force entirely comparable with that given bytetryl loaded and fired under the same conditions.

While I have described my process in detail only as a plied to thecondensation and nitration of dmitrochlorbenzcne and ethylene glycol, itis understood that other nitrochloro aromatic compounds, such, for example, as dinitrochlo-rotolueaie, may be used, as well as variouspolyhydric alcohols other than those specifically mentioned above. Myprocess is also not confined to the particular method of condensation ornitration given in the specific example.

I claim: 7

1. A process or producing an explosive compound which comprisescondensing a polyhydric alcohol, having not more than 3 'hydroxylgroups, with a. nitro-chlor aromatic compound and nitrating the productof condensation.

2. A process of producing an explosive compound which com risescondensing a glycol with a nitro-c lor aromatic compound and nitratingsation. 7

3. A process of producing anexplosive compound which comprisescondensing ethylene glycolwith dinitrochlorbenzene and nitrating theproduct of condensation.

4. A process of producing an explosive compound whichcomprises'nitrating the product obtainable iby the condensation of aglycol with dinitrochlorbenzene.

5. A process 'of producing an explosive compound which-comprisesnitrating :the product obtainable by condensing ethylene glycol with 2,4-dinitrochlorbenzene.

6. A process of producing an explosive the product of condencompoundwhich comprises nitrating dinitrophenoxy-ethanol. Y

'7. An explosive comprising an organic compound of the aromatic series,having a plurality of nitro groups attached to the ring and a side chaincomprising a mono nitrate of an aliphatic alcohol attached to the ringthrough oxygen.

8. An explosive comprising a nitro-eryloxy-alkyl nitrate.

9. An explosive comprising a'polynitrophenyloxy-alkyl nitrate.

10. An explosive comprising the compound obtainable by nitrating theproduct resulting from the condensation of a glycol containing less thanfive carbon atoms with a nitro-chlor aromatic compound of the-benzeneseries. v

11. An explosive comprising a nitrated dinitrophenoxy-ethanol.

12. An explosive comprising trinitrophenoxy-ethyl nitrate.

In testimony whereof I aflix my signature.

. HAROLD A.-LEWIS.

